From Villain to slave
by evildragonlord101
Summary: Jessie seeks to take revenge on Ash for her many defeats over the years by taking what he loves the most...his mother. However things soon turn in ways that the evil villainess would have never guessed.
1. Chapter 1

From Villain to Slave

"Hi mom!" Ash Ketchum said greeting his mother after his long travels in the Kalos Region.

"Oh Ash, welcome home sweetie!" Delia Ketchum said hugging her son tightly happy to have him back home. "How was your trip in Kalos. Did you meet anyone special?" Delia asked teasingly causing her son to blush.

"Well actually yeah I have." Ash said rubbing The back of his head recalling his final moments with Serena after he left for home.

"Well then I can't wait to hear all about her. Why don't you go to your room and rest up." Delia said with a smile Ash nodded while Pikachu jumped off his shoulder as his partner walked up to his room.

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Ash closed the door to his room and set down his back pack as he laid down in his bed. "It feels good to be home again." Ash said before he felt something begin to nuzzle at his legs and smirked.

"Did you miss me too?" He asked as he sat up to see The figure in front of him, a woman bound in a kneeling position with several black leather straps and a black leather armbinder. Her mouth was forced oped by a wide metal ring gag, and her hair was concealed under a black leather hood that covered so but her nostrils and exposed her runny red lips. Ash smiled as he pets her head earning a car lay purr from the woman before she nuzzled her head against his crotch area. "Oh so my little pet is hungry eh?" Ash said as he stood up and unzipped his pants

"MMMPH!" The woman moaned as she wrapped her lips around the cock and pushed it all the way in and began to suck in Ash's manhood.

Ash watched the bound beauty pump the cock deep into her mouth with low slurps and grunts. He could feel her tongue licking around the cock, increasing his pleasure.

Her sucking became more and more passionate as her body was filled with heated lust. Her whole body was throbbing and aching with heated lust. She clamped her lips around the cock and gave it a long hard suck. She sighed as cum filled her mouth. The bound beauty happily gulped down the seed and then went back to her blowjob. She was rewarded with another mouth full.

"Wow, you've gotten better, You must have really missed me." Ash said as he reached up and yanked off the woman's black leather hood to reveal a woman with short magenta hair her with dull purple eyes, her tongue hung out panting heavily. "I missed you too...Jessie." And it was true the woman in her knees sucking him off was none other than Jessie former member of Team Rocket.

As she continued suck off The young teenager she couldn't help but think back to the chain of events that had led her to this moment, she had it all planed so well.

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One month ago

Jessie walked out the shower with an angry look on her face. She had never been more angry in all her life then she was now. Having yet another failed attempt at capturing the twerp's Pikachu which resulted in her falling in a pile of mud. But what really got to her was how both Meowth and James had decided they had enough with being with members of Team Rocket and decided to quit. She couldn't believe how The two of them could just walk out on all that they had worked for all these years. The more she thought The more her thoughts fell on the same brat who had defeated, and humiliated them for 5 years. Ever since that day in the Pokemon Center that twerp had made them the laughing stock of The criminal underworld. There boss treated them like garbage and they comrades treated them like a joke. And she was done with it.

"That twerp is going to pay for all these years of humiliation! I swear it!" Jessie vowed slamming her fist down on her nightstand before a smirk crept up on her face. "And I know just how to do it." The villainous vixen said as she pulled up a picture of Ash and his mother.

"If I get my hands on the twerp's mother he'll have to do whatever I say, including handing over all his Pokemon." Jessie said with a sinister smile.

She tossed the robe onto the bed and stepped into her walk-in closet, stopping to study the clothes on the racks on shelves. A lacy black bra and thong were all that cover her voluptuous body. She picked a pair of black spandex pants and squeezed her lower body. The pants were so tight you could almost see the crack in her firm round ass. Next came the matching spandex top, she bit her lips as she tugged it over her more than ample bosom. She slipped on her only pair of black sneakers, walked out to her bedroom and stopping in front of her vanity table to brushed back her long magenta hair and tied it back with a black ribbon. She studied the effect and nodded.

"Time to get to work." Jessie said as she picked up the small leather case that contain her burglar tools.

The moonlight shined over the peaceful town of Pallet. However while the town's folk slept comfortably in bed a black clad figure crept through the night unroll she came to small house with an outdoor garden. Jessie smiled and pulled out her lock picks. Lois studied the lock and slipped one of the picks into the slit unlocking the door.

She slowly crept into the Ketchum home and made her way up the stairs until she came to two rooms. She was unsure which room belonged to twerp or his mother. Deciding to take a chance Jessie opened the first room on the right. As she walked in she found a room with a poster Lance battling against Cynthia beside a case containing badges from the Kanto, Jhoto, Hoenn, and Unova region along with the Battle Frontier Symbols. It didn't take her long to realize this was the tower's room.

"Jeez guys he's just a kid after all." Jessie chuckled as she walked around the room eyeing Ash's badges. "Bet I could sell these for a good chunk of change." Jessie quickly pulled the cases off the wall before unzipping her bag stuffing all 4 cases inside.

"Now let's pay mommy a...AIIIIIIIIIIIIIIIIII!" Jessie screamed as an electrical shock hit her body, sending her flying back against the wall. She groaned and slid down onto the floor in a daze. She felt herself slipping away and groaned.

"Well this is a surprise i wasn't expecting any guess today." That was the last thing Jessie heard before she passed out.

Standing over her was none other than Delia Ketchum with her trusty Mr. Mime his hands cracking with electricity from the shock wave attack he used on Jessie.

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The first thing that Jessie realized when she awoke was that she was on her knees. The second thing was the taste of a rubbed bit that was shoved into her mouth and locked behind her head. As she became more aware, she looked down and saw that she was no longer wearing anything of her own. Instead she had been stripped and was now wearing a black leather harness with silver studs locked around her waist with half cups that lifted her tits, making them look huge and perky. Her hands were pulled behind her back and bound to the back of the harness with what felt like steel rings. The final humiliation was a thick leather collar that was wrapped around her neck. A silver chain dangled down between her heaving tits.

The bound beauty looked around and studied the room. There was a four-poster bed with a flowered quilt on it. A padded bench sat off to one side.

"Well it looks like our little cat-burglar is awake." Jessie turned her head to see the woman she had come to kidnap standing behind her.

The Ketchum mother was wearing red leather hip boots and opera gloves. A black and red leather corset lifted her boobs making the look huge. A leather hair band kept her thick mane out her face but allowed it to flow over her shoulders and back.

"I'm so glad that your awake, things just wouldn't be as fun if you were asleep." Delia said walking up to Jessie with a riding crop in her hands.

"Lmmmh Mmmmh Gmmmm!" Jessie screamed through her gag glaring at Delia. Then she felt a powerful slap across the left side of her face, and she fell to the floor on her right.

"We'll have to work on that mouth of yours honey. Soon all it'll be good for is taking in my son's cock, along with your ass and pussy." Delia giggled.

"MPHHHHH!" Jessie screamed through her gag as she violently shook her

Delia wagged her finger in Jessie's face as she shook her head. "Oh no,no,no. This is your future. Consider this payback for all the time you've spent hunting my son and Pikachu. I don't take appreciate it when people threaten my son. So I'm going to make sure you repay him by becoming his faithful salve." Delia said in a deep dark menacing tone completely different from her usual sweet and gentle one.

"Now I think the first thing you'll do is put that tongue of yours to good use." Delia walked up to Jessie and unzipped The front part of corset exposing her wet dripping pussy to The bound villianess.

Jessie glared at Delia and shook her head defiantly.

Delia smiled seeing Jessie defiance. "I was hoping for that."

Jessie shot daggers with her eyes as she swore through the gag. She grunted as Delia grabbed her by the leash and began to pull her over to the padded bench.

"Crawl my little slave!' Delia laughed as she whipped her ass, "Crawl for me!"

"AW! AW! AW!" Jessie yelped, as she was force to crawl on her knees across the room. It took four lashes to make her bend over the seat. She glumly knelt there as she was fastened down with a thick belt.

Delia quickly spread her legs and locked them to the base of the bench. She gave the magnificent ass a pat and then began to whip her ass.

"AUGHHHHHHHH!" Jessie screamed as the crop lashed her ass. Huge tears filled her eyes and streamed down her cheeks. She tried to sit up but her bondage held her in place. The shapely red-head wept like she had never wept. Her ass felt like it was on fire. She strained against her bonds but there was no escaping her punishment.

Delia stopped her whipping and studying the red striped ass. She leaned down and gave it a kiss. "Okay, bitch," She snapped, "Now I can move on to your tits and pussy or you can put that sweet mouth to work on my pussy."

Jessie tried to look defiant but sniffing back her tears didn't help. The bound beauty arched up and wailed in shock and horror as the leather crop lashed across her tits. In seconds she was screaming and sobbing as Delia whipped her tits.

"Okay, that enough for the boobs," Delia panted, "Now for the pussy."

"NAWWW!" Jessie squealed through her gag.

"What?" Delia asked. "What is that? You ready to lick my pussy?"

Jessie frantically nodded her head as she blinked away her tears.

Delia walked up by her head and took off the gag. She traced her face with the tip of the crop.

"Now you were saying?" Delia smiled.

"All right, all right, you bitch," Jessie snarled, "I'll lick your pussy but know this I will hunt you down…..OWWWWW!"

Delia brought the crop down across her pussy and grabbed her captive by the hair. She twisted her head back.

"I don't like your attitude," She growled, "It needs adjusting. More whipping is needed."

"NO! NO! I will lick your pussy. I will lick your pussy…mistress."

Jessie almost choked on the words but kept begging to lick her pussy.

"Excellent," Delia said, "Now stick out that tongue, my pet."

Jessie gulped forcing down her anger and stuck out her tongue.

"Perfect," Delia cooed as she threw her leg over her captive's head and pressed her crotch down on her mouth.

"OHHHHHHHH!" Delia sighed, "OH YOU SWEET BITCH! YOU HAVE BEEN WASTING YOUR TALENTS. LICK ME YOU SLUT, LICK ME!"

"Mmmmmph!" Jessie moaned as she stuck her tongue into her slit and worked it around. Delia's squeals of joy filled her ears as she continued to lick out her pussy.

"OH SWEET MEW!" Delia screamed as she climaxed. She grinded her pussy down into her captive's face. "OHHHHH! RIGHT THERE! OH! OH! YESSSSSSSS!"

Jessie licked and sucked on the pussy with loud slurps, making the bitch climax over and over. She was thrilled when the pussy was pulled away. She watched Delia walk over to the cupboard and take down a strap on. The dildo mounted to the leather belt was huge with small bumps on it.

"You, you…can't," Jessie sobbed, "Please. I have money I'll pay you, I'll leave your son alone. "

"I'm afraid I can't accept you generous offer, you see my son's a growing young man. And I want him to have something to help him when he finally decides to take that big step. And given you history your just the perfect specimen. A fine 25 year old girl, perfect hips, a good pair of d-cup's and nice firm ass that's just begging to be fucked. I'm sure after I'm done training you you'll come to enjoy my son's dock since its the only thing you'll every know." Delia said as she walked up behind.

"No don't do this pl-Mmmmph!" Jessie please were cut off as Deila strapped the bag back in her mouth effectively silencing her once again.

"AIIIIIIIIII!" Jessie screamed as the hard plastic cock pushed into her tight pussy. She arched up and wailed as her captor began to pound his the sex toy in and out.

Delia arched up and ground the dildo deep into her captive. She grinded the sex toy around savoring her domination over this supposed villainess. She grabbed onto her tits and dug her nails into her tits.

"AUGHHHHHHHHH!" Jessie screamed, as her tits were abuse while the hard plastic cock slammed in and out her pussy. The bound beauty strained against her bonds as her body still hot from the last assault. Her body began to burn like it was on fire.

The red-haired beauty fucked the gorgeous villainess with al she had. Delia felt the sweat begin to form on her body and loved the feel of it. He lowered her mouth and began to suck on her big tits while mashing them around.

"UGH! UGH! UGH! Jessie panted and sobbed as her body was violated. She closed her eyes and squealed as an orgasm slammed into her. The bound beauty gasped in delight, She was just getting over the first orgasm when another one hit.

Delia gave her a couple good hard fucks and then pulled out. She took off the strap on and moved up onto her chest. She blew the struggling villainess a kiss.

"Time for you to give me something, my little whore." Delia panted as she took off the ball gag then stepped in front of Jessie spreading her butt cheeks exposing her her pussy and anus.

"My ass, whore." Delia snarled, "Lick it! Now bitch!"

Jessie whimpered as she lean forward and pushed her face into the firm round ass. She stuck out her tongue and began to lick the ass. Jessie wretchedly began to rim her butt with her tongue. The defeated blonde ran her tongue up and down the rim and them clamped her lips over the butt hole. She sucked and licked the ass with loud slurps.

"OHHHHHHHHHMYYYYY!" Delia gasped in delight as the talented whore kissed and licked her butt. She closed her eyes and enjoyed the mouth servicing her and the thought of the great Jessie of Team Rocket doing such a humiliating thing.

Jessie sobbed and whimpered as she darted her tongue in and out of her ass, wondering if this humiliation would ever end.

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"Oh Ash I'm so glade that your own your way home. I'm so sorry about what happened in the Unvoa League." Delia said as she walked around the bedroom, talking to her son. She had seen the results of the Unova League and was very upset to see he had lost once but she was just happy her baby boy was,coming home. Delia smiled as she leered over the naked blonde lying spread-eagle across the bed. Leather strips held her down. A leather bondage mask completely covered her head except for her mouth, nose and ears. Headphones were clamped over ears. Her ruby lips were wrapped around a ballgag. Two vibrators were plugged into the wall, buzzed away in her ass and pussy, making her come over and over.

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"MMMMMMPH! MMMMMPH!" Jessie pleaded. Delia ignored her, and continued to push the dildo in.

"Hold your butt steady, slut!" Delia ordered as Jessie shook her hips. She slapped her right buttock savagely, causing her to buck.

"If you don't cooperate, I'll use a bigger one." Delia threatened. Jessie stopped her wriggling at once, and only moan into her gag as Delia completed the insertion of the dildo in her, leaving only the knurled cap at the end of the shank outside the lips of her vulva.

Delia now stood up and went over to the row of anal plugs, lined up underneath the dildos. they seemed to have been arranged in sizes corresponding to the dildos above them. She took the one under the gap left vacant by the dildo now residing within Jessie's vagina. She applied a big Shelping of lubricant on the pointed rubber tip of the cone of the butt. She let it stand in his hand to let the goo slid down the cone to the flanged base of the plug. Replacing the tube on its rack, She rubbed the goo all over the cone and came around to Jessie's rear.

Jessie looked up at him, pleading with her eyes. her propped open mouth continued to drool, dripping saliva onto the floor below her. her slaver, of course, ignored her and knelt down behind her. Soon, sShe felt the tip of the cone being applied to the puckered mouth of her anus. SShe screwed her eyes shut at what sShe knew was coming next, as the point parted her sphincter and entered her.

As the cone advanced into her, its girth grew steadily. A shock shot up Jessie's spine as the sphincter reacShed its elastic limit. SShe threw back her Shead once more at the pain. her slaver eased off a little bit for a while, then renewed the advance of the cone, stretching her sphincter still further.

"MMMMMMMMPHHHHH!" Jessie moaned into her ball-gag, as another bout of pain shot up from her ass.

Delia eased off again, and let Jessie rest for a couple of moments, then, with one firm shove, She pressed the plug in all the way until the sphincter closed over the flanged base, eliciting one final gagged moan from the enslaved feline bandit. SShe could only shake her Shead at the pain, panting and perspiring.

"Don't drop those now," Delia warned, "Otherwise, I would just have to put in something bigger." Jessie stood silently as Delia wakes over to the dresser.

Delia retrieved an electric shears from the drawers. Jessie's eyes opened at this, but she could do little to resist as the other woman came up to her and switched on the razor. It did not take long for Delia to cut the long raven black locks of Jessie's hair, leaving a short magenta buzz-cut behind.

Delia took a handheld mirror and held it before her face to see her new haircut. She had to admit it was not too bad, actually. In fact, it reminded her of her androgynous haircut when she was a professional dominatrix in her younger years.

"Now that you've got your new look it's time for you to learn where you stand from now on." Delia said with a sinister grin as she held up a leather hood before applying it over Jessie's head.

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"Ash! Welcome home!" Delia exclaimed hugging her son.

"Hey mom it's good to be home." Ash said to his mother.

"I was just about to cook dinner, why don't you go and freshen up. I have a special surprise for you." Delia giggles while Ash gave her a confused look as he walked up The stairs to his room.

When the young 16 year old opened the door he was greeted with an unexpected sight. Kneeling in front of him was a woman dressed in black skin-tight catsuit with slits cut open exposing her breasts as well as her pussy and anus her crimson red lips were spread over a large red ball-gag as drool leaked onto his sumptuous bosom. He nostrils flared over the think black leather bondage hood that covered all but her mouth. She looked around vigorously crawling on her knees till she came to a stop in front of Ash and nuzzled her head against the front of his pants.

"Isn't she beautiful." Ash turned his head to see his mother standing behind her giggling as she covered her mouth with her hand to hold back her giggles. "It took a few days but she's now the prefect pet don't you think so Ash?"

"M...Mom?! What's going on!?" Ash nearly screamed before pointing to the bound beauty in front of him. "Who is this woman!? What did you do to her!?"

Delia sighed she knew this would be her son's reaction. "Ash your a sweet boy, growing up to be a fine young man. But I feel that if your ever going to settle down and get married or at the very least have a girlfriend you should have something to help you get a start." Delia explained before she motioned over to the captive woman in front of them. "That's what this fine beauty is for, she's your new Fuck-Toy, your living sex-doll, a precious slave to help you please and satisfy your every erotic desire."

"But mom this is..." Ash was cute off as his mother gently silenced him with a kiss to the lips. She's eyes widened a bit as he felt a strange sensation wash over good body. "Now my little boy go and become a man." Delia said with a wink as she walked out the room leaving Ash alone with his new pet.

Ash turned around to see his new found pet moaning as she squirmed across the floor rubbing her legs together hoping to get some form of release.

"Well I guess I better make use of this gift." Ash said unzipping his pants which reached the woman's ears. She perked up and shuffled over to Ash sniffing around his long 10 inch cock. Ash unclipped her gag.

She then ran her tongue around the cock, coating it with her own spit. She worked down to his balls before a the bound beauty paused for a moment and then pushed her tongue over the twin sacs. She gave the balls a good tongue licking and then ran her tongue up to the head.

"Oh yeah, mmmmm." Ash sighed as she kissed and nibbled his cockhead

Jessie rolled her tongue over the pole while she gulped on it. She pushed the cock deep into her throat, held it there and then pulled it back. The shapely beauty increased her sucking when she felt the cock swell. Ash sat up and grabbed her head with both hands, holding it in place as he emptied his cock into her throat.

"AUGHHHHHH!" Jessie moaned as she swallowed down the boy's seed filling the mouth spilling out and dribbling down her chin as she greedily drank it down. Ash pulled her head back and strapped the back into place helping the woman up.

"Get on the bed, stick you ass up for me." Ash said giving her a firm slap on her right as s cheek.

"MMMPH!" Jessie cried out before she did as she was told sticking her as high up wiggling enticing Ash to fuck her.

"Well, well, well somebody wants a good ass fuck doesn't she?" Ash said rubbing her ass.

"Mmmhpmm! Mmmhmm! " Jessie said nodding vigorously. Ash walked up to her spreading her ass cheeks.

"Get ready." Ash said with a smirk as he moved his cock up against her hole. he gripped her hips and thrust his cock into her butt.

"MMMMMMPH!" Jessie screamed when she felt the long pole being pushed into her ass. She reared up as she felt his balls press up against her backside. The bound beauty began to grunt and squeal as the cock began to pump in and out her ass. "ACK! ACK! ACK! ACK!"

Ash panted as he reamed out her ass with his iron hard cock. He licked his lips as he savored the way her ass was crushing his cock. He increased his fucking ass and began to swat her ass.

"UGH! UGH! UGH!" The helpless woman grunted as the cock pounded her ass with the brutal force. She squealed each time the hand came down on her butt. She couldn't stop herself from pushing back against the cock as her own lust took control of her body.

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I can't stop myself! Please keep fucking me more and more!" Jessie screamed as Ash conitued to plow himself in her massive rear slapping her butt with each thrust.

I love your dick! Give me lots and lots of your yummy cum!" Jessie said as she ran her tongue lover his long ride before stuffing it into her mouth giving him yet another blowjob. 


	2. Chapter 2

Hey I've read some reviews and I've decided to let you guys decide who you want to enslaved nwxt

Domino

Hunter J

Cassidy


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